Similar to bungalows and two-flats, workers cottages were originally built as affordable housing and have since become an ever-present part of Chicago’s residential landscape. Unfortunately, it’s becoming harder to find this iconic building style around the city nowadays as these modest-sized homes are threatened all the time by new (and larger) developments. Organizations like the Chicago Workers Cottage Initiative are trying to shine a light on this vernacular architecture type, defined as one-and-a-half stories with raised basements, narrow stoops, and a front-facing gable roof. Constructed of various materials like brick or wood, most of these homes date from the 1870s through 1910. While not every workers cottage can be preserved and protected, hopefully the following homes will show you they’re charming and flexible designs. Some have been turned into duplexes, while others have been modernized. One even survived the Great Chicago Fire.

2121 N Hudson Ave, $2,395,000

One of the city’s best known residences to survive the Great Chicago Fire of 1871, the Richard Bellinger cottage was just two years old when it stood in the path of the conflagration. It was only saved because the owner ripped up the wooden sidewalk and supposedly wetted the roof with cider (although that might have been made up by a newspaper reporter). Some original features have remained over the last 153 years like the exterior’s frame clapboard siding with wood carved details and brick-and-stone base. While inside the living room is a brick wall with a two-sided fireplace. Designed by W.W. Boyington, architect of the pre-fire Water Tower, the current owners added a three-story section to the back of the historic structure, creating additional space that opens up to a private terrace full of trees and evergreen shrubs. 

2035 W Rice St., $899,000

Don’t let the stucco facade fool you, the historic interior of this Ukrainian Village workers cottage built in 1884 is nearly intact from the lovely wood trim to original built-ins. Open concept is the trend even in older homes, so I’m surprised actual walls survive here. Yet this three-bedroom, two-bathroom has some contemporary updates, which is apparent in the kitchen and bathrooms. But the best part is the property comes with a detached two-story coach house. Not only do you have a two-car garage, but above is an open-concept space with a loft bedroom. It’s a perfect opportunity for rental income (it’s currently rented at $1,800 per month). 

2064 N Leavitt St., $775,000

This two-bedroom, two-bathroom home in Bucktown is contingent, and you can see why! Recently gut rehabbed, the kitchen, bathrooms, walls, and mechanicals are all up to date, while the overall space feels light and airy. I personally love the modern touches, like the open wooden staircase that connects all the rooms together. The RT-4 zoned property also comes with a one-bedroom, one-bathroom coach house above the garage, an ideal place to turn into an Airbnb or a rental unit. 

1644 N Troy St, $899,969

In early 2021, this workers cottage sold for $355,000, which reflected value-priced homes in the Logan Square-Humboldt Park area over the last several years. Since then, the residence has undergone a modern makeover and jumped 154% with a current price tag of $899,969. Located just a block from the 606, where gentrification has been a hot-button issue for many local residents, the multi-unit building offers a number of possibilities as owners can live on the first floor while renting or hosting an Airbnb from the zoned in-law two-bedroom, two-bathroom upstairs suite that comes with its own private entrance.

1734 N Sedgwick St, $979,000

If you’re looking for a neighborhood full of picturesque 19th century workers cottages, look no farther than Old Town Triangle. Like the previous homes listed for sale, this one has been converted into a two-flat. It recently changed hands back in 2015. The fully rehabbed building offers a couple of possibilities: it can simply remain as it is or be converted back to a single-family home. The main floor rental space features two bedrooms and one bathroom, while the owner’s unit comes with three bedrooms, one bathroom, and a full family room in the back with access to your own private courtyard.